Trifluoroacetic acid → 5-Methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1020300Notes

Reaction equation

HRID 1020300 reaction equation
CO[CH2:3][N:4](CC1C=CC=CC=1)[CH2:5][Si](C)(C)C.[C:17](O)(C(F)(F)F)=O.[CH3:24][O:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[C:31](=O)[CH:30]=[CH:29]2>C(Cl)Cl>[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:32]2[CH:31]([CH3:17])[CH:30]3[CH2:5][NH:4][CH2:3][CH:29]3[C:28]=2[CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 110409905-Methoxy-1H-inden-1-one

Product 1

HCID 115429805-Methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (17.3 mL, 67.6 mmol) and TFA (3.4 mL) were added to a solution of 5-methoxy-inden-1-one (5.4 g, 33.8 mmol) in CH2Cl2 (165 mL) at 0° C. The reaction was stirred for 3 hours at room temperature and quenched with saturated aqueous NaHCO3 (165 mL). The organic layer was separated, washed with brine (100 mL), dried over MgSO4, and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C19H19NO2+H: 294, observed: 294.

Workup

  1. customquenched with saturated aqueous NaHCO3 (165 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5036b86c4b38415db7a3db5ce4a23eba
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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